I sit down with Sean Gannon, founder of GTMPPL (GTM People), to answer the "unanswerable" question: Who is Sean Gannon?. We dive into a refreshing take on sales leadership—why the best managers strive to make themselves obsolete—and explore the often friction-filled relationship between sales and marketing.

From the trenches of EdTech to the nuances of Sandler training, Sean shares candid stories about the transition from "spreadsheet inspection" to true coaching. We also discuss why "everyone sells" (even if they don't have a quota) and share a hilarious cautionary tale about what happens when a salesperson sticks to the script even after the customer has said "yes."

Key Highlights & Takeaways:

• The "Obsolete" Manager: Sean argues that a manager’s ultimate goal is to make themselves invisible and obsolete; if the team can't function without you, you aren't doing your job.

• Everyone is in Sales: Whether you are an SDR, a CSM, or pitching a project to your boss, everyone in the organization is selling something.

• Marketing vs. Sales: We dismantle the old school "throw it over the wall" mentality regarding leads. Sean emphasizes that while marketing provides air cover, they must care about close rates, not just lead volume.

• Coaching vs. Inspection: Sean opens up about his evolution from a manager who managed by spreadsheet to a leader who focused on coaching, which drastically improved his team's retention from 18 to 36 months.

• The Danger of the Script: A great lesson on reading the room—Sean shares a story where a salesperson kept taking him through the Sandler "pain funnel" even though Sean was already sold and ready to buy.

• Authenticity Wins: Why "I don't know" is a perfectly acceptable answer that builds more rapport than faking it.

  
  

Memorable Quotes:

• "I view my role as an executive or a sales manager... to make myself obsolete. Like, I should be relatively invisible as your manager." — Sean Gannon

• "Your job is to sell the meeting... not to sell the company, isn't to sell the solution." — Sean Gannon

• "The best sales enablement, you don't know what's being done to you. You don't know what's being done for you." — Lee Levitt

  
  

  Closing Thought:As Sean pointed out, the ultimate goal of a leader is to become "invisible"—building a team so competent and well-coached that they no longer need you to intervene. Are you managing by "inspection," looking for mistakes in a spreadsheet, or are you coaching for longevity?. This episode challenges us to stop hovering and start empowering

• Next Steps:If you are ready to build a revenue engine that scales (and maybe finally make yourself obsolete), go say hello to Sean.

  • Visit: GTMPPL.com

  • Connect: Find Sean Gannon on LinkedIn for his latest observations on the industry.

  • Listen & Subscribe: Don’t miss an episode of Thoughts on Selling. Hit subscribe wherever you get your podcasts!

In this episode, I geek out with Maeve Ferguson, an ex-steeplechase jockey turned Big Four consultant and data expert. We dive deep into the often-overlooked power of diagnostic assessments and how "Agentic AI" is revolutionizing the way experts build sales funnels.

Maeve shares how moving beyond simple "quiz funnels" to robust data diagnostics can uncover the gap between an entrepreneur's perception and their business reality, ultimately leading to higher-quality leads and closed deals.

Key Highlights & Takeaways:

• The Power of Diagnostics: Maeve explains why diagnostic assessments are superior to standard lead magnets. They provide proprietary data that allows you to segment audiences by investment ability (Platinum to Bronze) and customize the sales journey based on their specific struggles.

• Unicorn Leadership Types: We discuss the "Ulta" framework—Visionizer, Strategizer, and Mobilizer. Understanding these profiles is critical not just for leadership, but for ensuring your sales and marketing teams aren't operating at cross-purposes.

• Agentic AI in Sales: Maeve reveals how she uses AI agents to run continuously in the background. These agents analyze who buys high-ticket items versus low-ticket items and automatically optimize ad copy to attract better buyers.

• The "Delulu" Factor: Data hates nature and never lies. Maeve shares amusing insights on how diagnostics expose the gap between where business owners feel they are versus what the numbers actually say—a critical leverage point for sales conversations.

• Sales Coaching Automation: We explore how AI agents now review sales call transcripts against frameworks to provide immediate, in-context coaching to sales reps, celebrating wins and flagging missed opportunities.

• Passion, Authenticity, and Curiosity: I challenge Maeve on her self-assessment as a salesperson, applying my three-part diagnostic for sales effectiveness.

Resources Mentioned:

• Maeve’s Diagnostic: Impact Score Assessment

• Book Mentioned: Surrounded by Idiots by Thomas Erikson

Connect with Maeve Ferguson:

• LinkedIn: Maeve Ferguson

• Substack: Maeve Ferguson

This is one of the most high-energy, high-insight conversations we've had on the show!
If you care about data, diagnostics, sales, or the future of AI-powered selling, you’re going to love this one.

In this episode of Thoughts on Selling, I sit down with someone I truly consider a “brother from another mother” — Lester Sidney.

If there’s a theme for this conversation, it’s this:

👉 Sales is human work. And humans run on purpose, energy, trust, and honesty.

Lester discusses his 17-year tech sales career, a couple ofunexpected detours, and the journey that ultimately led him to rediscover his why: helping people see the potential insidethemselves that they can’t yet see.

What unfolds from there is one of the most honest, raw, and deeply human sales conversations we've recorded.

We talk about:

· Finding purpose when life knocks you flat, including Lester’s battle with depression after leaving a company he helped build.

· The Ikigai framework and how it helped him identify a deeper purpose rooted in mentoring and coaching.

· Energy as a magnet — how the energy we project determines the people and opportunities we attract.

· Why giving beats taking, and how “pay it forward” moments shape who we become.

· The sacred role of trust in sales, and why walking away from a deal can be the single biggest credibility builder you’ll ever have.

· Extreme Ownership — and why real leaders take responsibility for everything their team does. (Yes, this comes with stories.)

· Why vulnerability isn’t weakness — it’s a sales superpower. Lester is candid about how being open unlocks deeper relationships with customers.

· The compound effect, and why small improvements add up to big transformation — in fitness, in selling, and in life.

· Raising kids with mindset, from eliminating the word can’tto teaching his son that mistakes are how we grow.

· What Lester looks for when hiring sellers — and why coachable is the non-negotiable #1 trait.

This is an episode about selling, yes — but more importantly, it’sabout being human. It’s about showing up with authenticity, owning your story, doing the hard things, and leading with heart.

It’s one of my favorite episodes we’ve done. Give it a listen —and please tell me what resonates most with you!

In this episode of Thoughts on Selling, I sit down with my friend and long-time sales industry pioneer Gerhard Gschwandtner — founder of Selling Power Magazine and an enduring voice in the world of sales leadership, mindset, and authenticity.

Gerhard’s story is extraordinary — from growing up in Austria and stumbling into his first sales role (inventing sales enablement decades before it had a name) to creating Selling Power Magazine, one of the most influential platforms in the history of professional selling.

We talk about how curiosity, creativity, and courage shape every career — and how staying in the question, not rushing to the answer, is what keeps you growing. Gerhard shares how he’s helped shape the profession through interviews with legends like Mary Kay, Zig Ziglar, Wayne Dyer, Mark Benioff, and even a few time-travel guests like “Abraham Lincoln” and “Aristotle.”

This isn’t just a history of sales — it’s a masterclass in mindset.

💡 Key Takeaways

• “Who are you?” is the most important sales question. You can’t sell authentically until you know yourself.

• Mindset is everything. Gerhard outlines three lenses — implanted, imprinted, and inspired mindsets — that shape how we think and sell.

• Sales enablement started long before software. His early innovations — customer tours, training vignettes, and user groups — became today’s best practices.

• Authenticity builds trust faster than persuasion. Telling the truth, even when it’s uncomfortable, turns customers into lifelong advocates.

• AI is both a gift and a trap. Used wisely, it elevates preparation. Used poorly, it replaces thinking.

• The bigger the why, the bigger the try — and the easier the how.

This conversation spans history, psychology, and purpose — from Aristotle to AI — reminding us that great salespeople are first and foremost great humans.

🎧 Listen in and rediscover the timeless truth of selling: authenticity wins.

#ThoughtsOnSelling #SalesMindset #Authenticity #SellingPower #SalesEnablement #InnerGame

In this episode of Thoughts on Selling, I sit down with Lauren Bailey, one of the most dynamic voices in modern sales leadership. She’s the founder of Factor 8 (award-winning inside sales training), #GirlsClub (empowering women in revenue roles), and Legacy VIP (a community for seasoned executives who crave purpose and authentic connection).

What starts as a conversation about leadership quickly turns into something deeper — a raw, funny, and inspiring dialogue about who we are and why we do what we do.

Lauren shares how losing her best friend became the catalyst for creating Legacy, a space where executives show up as their whole selves — not just their résumés. She also talks about integrity, self-awareness, and the power of human connection — lessons drawn from personal experience, Landmark Forum, and years of leading sales teams worldwide.

• Show up and say yes. These two rules, says Lauren, change everything — in leadership, friendship, and sales.

• Be impeccable with your word. (A nod to The Four Agreements.) If you say it, do it — and say less if you can’t commit.

• Authenticity over perfection. Perfectionism kills confidence; authenticity builds it.

• Celebrate the 3 F’s — fears, failures, and f-ups. Vulnerability builds confidence faster than success ever could.

• Coachability matters. The best sellers aren’t perfect — they’re curious, confident, and willing to be coached.

• The pause game. Lauren’s favorite technique: pause a recorded sales call every 10 seconds and ask, “What’s the customer thinking?” and “What would you do next?” It builds awareness, empathy, and skill faster than any script.

• Leadership is a “we” sport. The skills that make us great sellers don’t always make us great managers. True leadership is about creating space — not taking it.

We talk about Landmark Forum, Don Miguel Ruiz’s The Four Agreements, and the difference between selling and buying. It’s a conversation full of laughter, truth bombs, and practical takeaways for anyone leading, coaching, or selling today.

Lauren’s energy is contagious — she’ll make you laugh, nod, and probably take notes.

🎧 Listen in and rediscover the joy in what we do — showing up, saying yes, and being fully human while we sell, lead, and live.

#ThoughtsOnSelling #SalesLeadership #AuthenticSelling #InnerGame #WomenInSales #SalesEnablement #LegacyVIP

🧭 Key Themes & Lessons

In this episode of Thoughts on Selling, I sit down with Kevin Hubschmann, a former enterprise software rep turned comedian and founder of Laugh.Events — a company literally delivering “Laughter as a Service.”

We dig into the parallels between improv, comedy, and enterprise sales, exploring how humor, presence, and curiosity can transform the way we connect with customers. Kevin shares his story of balancing daytime sales calls with nighttime comedy clubs, and how the two worlds collided to shape his philosophy on sales as performance and connection.

Key themes:

• Listening > Talking. Kevin breaks down why most sales calls fail because reps talk too much — and how mastering silence is the first step to earning trust

• F your good idea. (Yes, really.) In improv and in sales, the goal isn’t to deliver your rehearsed pitch — it’s to respond to what’s actually happening in the moment

• Yes, And… We explore how collaboration — not control — drives great sales conversations

• Callbacks in sales. Borrowed from stand-up comedy, callbacks create instant connection by recalling earlier details — proving you were listening and care

• Deliberate practice builds instinct. Sales mastery, like comedy, comes from reps — not scripts

• Laughter builds trust. Humor isn’t about cracking jokes. It’s a sign of shared understanding — the customer’s way of saying, “I get you”

We also talk about how curiosity creates genuine human connections — the kind that earn referrals and deepen relationships. From field sales to front-stage comedy, Kevin shows how the same skills that make people laugh also make people buy.

🎧 Tune in and learn how the best salespeople stay in the moment and create powerful connections

#ThoughtsOnSelling #SalesEnablement #Storytelling #AuthenticSelling #ImprovInSales #LaughterAsAService

In this episode of Thoughts on Selling, I sit down with Jake Isham — filmmaker, creative director, and founder of Creative Minds Agency.

Jake’s story is pure art-meets-entrepreneurship. He started as an actor, moved behind the camera to direct, and somewhere along the way became what he calls an “accidental marketer.”

We dig deep into the intersection of storytelling, sales, and authenticity — how great art and great selling share the same purpose: to create an effect. Jake explains how the best salespeople are actually performers — not in a fake way, but in the sense that they listen, adapt, and stay present in the scene.

Our conversation bounces between filmmaking, improv, and enterprise sales, but it all comes back to one central idea: sales is an art form. The goal isn’t to pitch harder or talk faster; it’s to create a feeling that sticks.

A few big takeaways:

• 🎭 Sales and acting share the same core skill — presence. Great sellers listen, improvise, and respond in the moment.

• 💬 Be interested, not interesting. Shift the spotlight to the customer; that’s where trust begins.

• 🧠 Reps build mastery. Like athletes and artists, salespeople get better through repetition and reflection — not theory.

• 🔥 Authenticity beats polish. When you lead with genuine curiosity and passion, selling stops feeling like selling.

• 🎥 Personal brand is leverage. Jake shows how documenting your story builds trust and visibility that lasts beyond any one deal.

• 💡 The right views matter more than viral views. You don’t need a million followers — you need the right audience.

• Jake and I also talk about the business of creativity — how he learned to blend craft with commerce, the value of expertise (“knowing where to tap”), and why every creator, seller, and leader needs to believe in what they’re offering.

  It’s a fun, high-energy conversation about where art meets revenue — and how showing up as yourself is the real competitive edge.

  🎧 Give it a listen, and let me know what lands with you.

  #SalesLeadership #PersonalBranding #AuthenticSelling #Storytelling #ThoughtsOnSelling